As I walked into Ao Po Grand Marina at midnight, the reality of where I was hit me as hard as the humidity on my skin. I had dreamt of this, of traveling halfway around the world to a foreign place with access to a sailboat and the confidence to sail it wherever my heart desired. It felt surreal walking down the damp docks, jiggling the keys in my hand, and grinning from ear to ear. My friends Rachel and Marjeanna had arrived earlier that day. “The boat is insanely nice, we’re feeling fancy,” they texted, after soaking up the views from the marina’s infinity pool all afternoon. I stepped aboard the Jeanneau Sun Odyssey 44 SV Keola Makani and quietly shuffled my bags into the forward berths, doing my best not to disturb my snoozing friends. Inflatable balloons dangled in the corner of the main salon. Rachel woke with a half-conscious grin and whispered, “Welcome to our yacht, captain; may your 40th birthday adventure begin!”

In January, I had pulled the trigger on securing a deposit for a highly discounted eight-day bareboat charter for my 40th birthday in May, which I would come to find is arguably the hottest and most humid time of the year. My goal was simple: recruit up to eight women to join me. I sent a detailed email invite to nearly 50 whom I knew from all walks of life; it didn’t particularly matter to me if they had sailing experience, just that they were willing to go. I yearned to challenge myself as an international bareboat skipper; to “enjoy boats again” (preferably one I didn’t own). The only caveat was: no kids, and no men.

Don’t get me wrong, I thoroughly enjoy sailing with my guy friends (and absolutely adore kiddos), but there’s just something incredibly special and empowering about being on a boat with only women, as it so rarely happens. In my experience, women communicate differently, problem-solve differently, and generally challenge one another, well, differently. What I hadn’t considered is how over-committed they are at 40 compared with 20, now juggling jobs, pregnancies, partners, etc. The one crazy enough to join me was my former colleague Rachel, and we soon extended the invitation to her friend Marjeanna. Outside of a quick crash course led by yours truly, both had minimal sailing experience. I had only met Marjeanna once, but we seemed to get along well; I knew they were both capable, open-minded and most importantly, willing to go.

Continue reading in the November issue’s World of Chartering.